Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan, Hunan 411105, People's Republic of China.
J Agric Food Chem. 2020 Mar 4;68(9):2684-2695. doi: 10.1021/acs.jafc.9b05966. Epub 2020 Feb 21.
Dioxyethene fragment (-(OCHCH)-) was introduced into traditional alkyl β-d-glucopyranosides to ameliorate the water solubility, and eight nonionic surfactants, that is, alkoxy ethoxyethyl β-d-glucopyranosides with alkyl chain lengths ( = 6-16), were synthesized and characterized. Their hydrophilic and lipophilic balance number, water solubility, critical micelle concentration (cmc), γ, Γ, and hygroscopic rate decreased with an increase in the alkyl chain length. Hexadecoxy ethoxyethyl β-d-glucopyranoside had no water solubility at 25 °C. Decoxy ethoxyethyl β-d-glucopyranoside had the best emulsifying property in the toluene/water and -octane/water systems and the strongest foaming property, whereas dodecoxy ethoxyethyl β-d-glucopyranoside had the best emulsifying property in the rapeseed oil/water system. Such β-d-glucopyranosides ( = 6-12) exhibited excellent surface activity. In addition, for the binary mixture of alkoxy ethoxyethyl β-d-glucopyranosides ( = 8, 10, 12) and sodium dodecyl sulfate or cetyl trimethyl ammonium chloride, their cmc values were lower than the pure β-d-glucopyranosides, indicating that they had synergistic interactions. The fan focal conic textures of alkoxy ethoxyethyl β-d-glucopyranosides ( = 7-16) were observed during the cooling process under a polarizing optical microscope. Alkoxy ethoxyethyl β-d-glucopyranosides ( = 14, 16) had the related melting points and the clear points with differential scanning calorimetry. With β-d-glucopyranosides ( = 6-16) and -butanol as the surfactant and cosurfactant, respectively, and with cyclohexane as the oil phase, the related microemulsion areas in their pseudoternary phase diagram system were investigated with the visual observation at 25 °C. Along with the slashing requirements of petroleum consumption, environmental protection, and green and sustainable development, nonionic sugar-based alkoxy ethoxyethyl β-d-glucopyranosides should be expected to have their potential practical application because of their strengthened hydrophilicity, improved water solubility, and enhanced surface activity.
二氧杂环己烷片段(-(OCHCH)-)被引入传统的烷基β-D-吡喃葡萄糖苷中，以改善其水溶性，合成并表征了八种非离子表面活性剂，即具有烷基链长（= 6-16）的烷氧基乙氧基乙基β-D-吡喃葡萄糖苷。它们的亲水亲油平衡值、水溶性、临界胶束浓度（cmc）、γ、Γ 和吸湿性率随烷基链长的增加而降低。十六烷氧基乙氧基乙基β-D-吡喃葡萄糖苷在 25°C 时没有水溶性。癸氧基乙氧基乙基β-D-吡喃葡萄糖苷在甲苯/水和-辛烷/水体系中具有最佳的乳化性能，泡沫性能最强，而十二烷氧基乙氧基乙基β-D-吡喃葡萄糖苷在菜籽油/水体系中具有最佳的乳化性能。这些β-D-吡喃葡萄糖苷（= 6-12）表现出优异的表面活性。此外，对于烷氧基乙氧基乙基β-D-吡喃葡萄糖苷（= 8、10、12）与十二烷基硫酸钠或十六烷基三甲基氯化铵的二元混合物，其 cmc 值低于纯β-D-吡喃葡萄糖苷，表明它们具有协同作用。在偏光显微镜下观察到烷氧基乙氧基乙基β-D-吡喃葡萄糖苷（= 7-16）在冷却过程中的扇形焦点共焦纹理。烷氧基乙氧基乙基β-D-吡喃葡萄糖苷（= 14、16）具有相关的熔点和差示扫描量热法的澄清点。用β-D-吡喃葡萄糖苷（= 6-16）和正丁醇分别作为表面活性剂和助表面活性剂，环己烷作为油相，在 25°C 下用目视观察研究了它们的伪三元相图体系中的相关微乳液区。随着石油消耗、环境保护和绿色可持续发展的严格要求，非离子糖基烷氧基乙氧基乙基β-D-吡喃葡萄糖苷有望因其增强的亲水性、改善的水溶性和增强的表面活性而具有潜在的实际应用。
